Ubers and Parolees
by flinkerdoodle
Summary: Prompt: My parole officer was called in for an emergency and he's usually my driver but now I have to call an Uber so I can get to work and I absolutely cannot miss a day of work but I'm legally obligated to tell you I'm a parolee please just drive me, I'm already late for work? (Destiel Oneshot/possibly more)


**Notes: Forgive me for any mistakes on the accuracy of Ubers or parolees!**

Dean impatiently tapped his foot on the curb outside his apartment. He'd been out there for nearly 45 minutes in the freezing cold air and had already called two Uber drivers, the first having legally denied driving him to work. He was already an hour late and if he missed a day of work, he was almost certain to lose his job, something he couldn't afford to happen.

After what felt like hours of waiting, an Uber car pulled up, a blue Ford Fiesta rolled to a slow stop. Dean sighed to himself and hastily prepared a speech mentally before pulling the back passenger door and ducking his head in.

"You're legally allowed to deny me a ride, but I'm obligated to tell you I'm a parolee and my officer isn't here but I need a ride to work and I can't miss a day or I'll lose my job and I'm already really late so please-" His professional speech flew out the window and he let out the spiel in one breath, cutting himself short and looking at the driver with what was hopefully a desperate look.

Dean couldn't get a good look at the driver, the rising sun halo-ing the around their face, denying Dean any details, but he could see them cock their head to one side.

"Sir," -a gravelly voice answered, definitely male- "I'll drive you, you don't need to worry."

Dean let out a breath he didn't realize he was holding and slipped into the back seat, setting his bag into the seat next to him. "Thank you sir, I'm sorry for being so pressuring, I just can't afford to lose my-" He started but stuttered as he caught a glimpse of the man in the driver's seat. "j-job," he finished, observing the mussed up hair and angular face of the smaller man. The sight was almost... refreshing if Dean was being honest with himself.

"Do not worry, um..."

"Dean," he finished for him.

"Dean. It's alright. You don't seem dangerous to me. My name is Castiel," the dark man said slowly as if he was thinking out every word in his head. Dean allowed himself a small, barely-there smile, cocking his head at the strange man's words.

"Nice to meet you Castiel," he said, leaning back in his seat to adjust the seatbelt as they turned at a stop light.

They were silent for a while, the quiet not uncomfortable as they drove along the highway. Then Castiel cleared his throat, his eyebrows pulling together in the rearview mirror and he started, "Um, forgive me if this is out of line," he rumbled, "but may I ask what you're on parole for?"

Dean bit the inside of his cheek. It wasn't an uncommon question, and this man had asked in a way that was nicer than most people, but he hoped he wouldn't scare the man in a way that would lose his only ride to work.

Dean scratched the back of his head, pinching his lips together and humming as he thought of a good way to put it. "Well," he began, "my younger brother has asthma, and when we were kids- "he paused, scrunching his eyebrows. "Well, let's just say my father wasn't a great parent. He didn't get my brother the medicine he needed, usually. And then one day he just didn't come home for a few days, and Sam was running really low on his meds-" He stopped again, hoping he wasn't blabbing too much and looked at the driver's face in the mirror. The man nodded his head, letting Dean know he wasn't being too overcoming.

"Well, I went to the drugstore. I was hoping I could just grab his prescription since I was related to him, but the lady said they needed my dad there and I just- I pretended to leave and when she wasn't looking, I just took it from behind the counter." He paused again, frowning at his own words. Castiel waited for him to finishing, glancing at him through the mirror. He continued. "I stuffed it in my bag and started walking back to the motel- we didn't even live in a house- but I heard someone yelling at me to stop and I just walked faster and then I just ran. I didn't even know what I was thinking. I was just so scared and-" Dean sighed. "I got to the room, but the police stormed the place and jeez, I don't even know what I was thinking but I grabbed my dad's gun- the one he gave me for 'safety-'" He put air quotes around it, because even he knew that was horribly stupid- "and I pointed it at the damn cops. Got me a few years in juvy and about a year in prison once I turned eighteen."

He looked at Castiel, expecting a grimace or fearful eyes, but he was surprised to be met with curious eyes. He was starting to enjoy that sliver of the man's face more and more.

"Well," Castiel started, talking as carefully as before, "that was much less... disturbing than I imagined it'd be."

And that had Dean laughing before Castiel could apologize, giving the dark haired man a bewildered face at the response. "Sorry man," Dean said between laughs, "I've just never really had that response before."

Castiel shook his head, eyes still squinted in confusion. "I do not understand what is so humorous about my response," he said quietly. Dean just smiled and slouched in the seat, feeling much more comfortable than before.

"So Castiel," Dean asked, "since you got part of my story, can I ask why you're so damn comfortable with driving a criminal around town?"

Castiel cleared his throat for the second time since the start of their drive. "Firstly, I am in control of this car, which makes you much less dangerous," he said matter-of-factly. "And you are obviously not dangerous if you're on parole. That usually means you have good behavior, correct?" He looked pointedly at Dean.

Dean couldn't help the small smirk forming on his face. "Yeah, that's pretty on the nose," he chuckled, noticing for the first time a five o'clock shadow on Castiel's face. "Nothing gets past you, Vizzini."

Castiel scrunched his eyes again. "I don't understand that reference."

Dean's mouth hung open in surprise. What kind of rock do you have to live under to _not_ see _The Princess Bride?_ He shook his head, trying pretending he didn't hear the blasphemy from the smaller man. He was about to express his surprise when he noticed blue eyes dragging over his tattoos peeking out from his sleeves and neck collar. He had to keep himself from chuckling as he spoke.

"Like what you see?" He said with raised eyebrows and a faint smirk. The crystal eyes darted away from Dean's gaze as he spluttered and ran a hair through his already thoroughly messy hair.

"J-just curious, my apologies-" he began.

"No worries," Dean interrupted, "just teasing."

The ride went silent again. It wasn't long till the two of them would arrive at the mechanics shop that Dean worked at. They had already talked away 20 minutes of the 35 minute driving time.

"So uh Cas- err, I mean Castiel," Dean stuttered, surprised at his own inability to speak, "tell me something about yourself." Dean wasn't sure why the hell he said that. Does it really matter?

Dean was surprised to see thoughtful eyes in the rearview, rather than judging, and he heard Castiel hum. "Hmm. I have several siblings, does that interest you?" Dean raised an eyebrow, prompting him to continue. "I have four brothers and a sister," he finally finished.

Dean couldn't hide the surprise on his face at that bit of information. "Are you a middle child or the baby?" he asked before he could stop himself.

"What makes you think I'm not the eldest?" Castiel asked with- was that a pout?

Dean chuckled. "Call it an educated guess."

Castiel carded through his hair once again, huffing. "I'm the youngest of the six of us," he mumbled over the hum of the car.

Dean tried not to laugh for Castiel's sake, but he felt a few deceitful chuckles escape and he apologized. "Sorry, Cas- fuck - Castiel-"

It was Castiel's turn to chuckle. "You can call me Cas if you like."

Dean liked seeing that smile on the dark haired man's face, he decided.

It was at that moment that Cas pulled into the dirt driveway to Singer's Auto. Dean pulled a few extra dollars' tip from his wallet, scribbling his number on one of the bills after battling internally whether he actually should do it.

"Oh, Dean you don't need to-"

"Keep it, please? And maybe call me sometime?" Dean asked, smiling a bit and shoving the wad of cash in Castiel's face. The driver opened his mouth to protest but ultimately found himself unable to deny cash in that manner.

Dean let a smirk replace his smile as Cas took the bills hesitantly. He winked at the mirror once, saying a "see you around" before grabbing his bag and exiting the car, leaving a slightly bewildered Castiel.

 **Notes: Be sure to leave comments on what you liked (or didn't like)!**


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